141684-48-2

Upstream product

• 141781-17-1 2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine 
• 117174-40-0 (2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile 
• 141684-44-8 1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>thymine 
• 117174-33-1 1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 141781-18-2 <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 

Downstream Products

• 141684-49-3 <1-<5'-O-(tert-butyldimethylsilyl)-2'-deoxy-β-D-erythro-pentofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 

Relevant academic research and scientific papers

TSAO derivatives: Highly specific inhibitors of human immunodeficiency virus type-1 (HIV-1) replication

TSAO derivatives represent a unique class of nucleosides that are specifically targeted at HIV-1 RT. This overview is focussed on the chemical synthesis, the conformational studies, the antiviral and metabolic properties of TSAO derivatives, as well as th

Synthesis of {1-[2',5'-bis-O-(t-butyldimethylsilyl)-β-D-xylo- and β-D-ribofuranosyl]Thymine}-3'-spiro-5''-{4''-amino-1'',2''-oxathiol e-2'',2''-dioxide} (TSAO). A novel type of specific anti-HIV agents

Reaction of O-mesylcyanohydrins of furanos-3'-ulosyl thymine with bases afforded β-D-xylo- and ribo-3'-substituted nucleosides. 2'-Deoxygenation of the selectively 5'-O-protected nucleoside gave the ribofuranosyl derivative of thymidine.

3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: Synthesis and antiviral activity of [2',5'-bis-O-(tert- butyldimethylsilyl)-β-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino- 1'',2''-oxathiole 2'',2''-dioxide] (TSAO) pyrimidine nucleosides

A series of 3'-spiro nucleosides have been synthesized and evaluated as anti-HIV-1 agents. Reaction of O-mesyl-cyanohydrins of furanos-3'-ulosyl nucleosides with base afforded [1,[2',5'-bis-O-(tert-butyldimethylsilyl)-β- D-xylo- and -ribofuranosyl]]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole 2'',2''-dioxide] derivatives of thymine, uracil and 4-N-acetylcytosine 11 and 12. Desilylation of 11 and 12 gave the full deprotected 3'-spiro xylo- and ribofuranosyl nucleosides 13 and 14 or the partially 5'-O-deprotected-3'- spiro β-D-xylo- and -ribo-nucleosides 15 and 16, or 2'-O-deprotected-3'- spiro β-D-ribo-nucleoside 17. 2'-Deoxygenation of 17 afforded 2'-deoxy-3'- spiro β-D-erythro-pentofuranosyl derivative 18. These 3'-spiro derivatives were evaluated for their anti-HIV-1 activity. All 3'-spiro nucleosides having a xylo configuration did not show any anti-HIV-1 activity. 3'-Spiro ribo- nucleosides with none or only one silyl group at C-2' or C-5' or the 2'-deoxy derivative were also inactive at subtoxic concentrations. However, 3'-spiro ribo-nucleosides having two silyl groups at C-2' and C-5' were potent and selective inhibitors of HIV-1. None of the nucleoside analogues that showed anti-HIV-1 activity proved inhibitory to the replication of HIV-2 or SIV.